柬埔寨柯拉斯那沉香的化学成分研究

该文采用ODS、硅胶、Sephadex LH-20等柱色谱技术,对柬埔寨野生柯拉斯那沉香(Aquilaria crassna)进行了研究。结果表明:从柬埔寨柯拉斯那所产沉香的乙醇提取物中进行分离共得到了10个化合物,包括一对对映异构体(9a/9b)。经波谱解析分别鉴定为6-甲氧基-2-[2-(3-羟基-4-甲氧基苯)乙基]色酮(1)、6-甲氧基-2-[2-(3-甲氧基-4-羟基苯)乙基]色酮(2)、6,7-二甲氧基-2-(2-苯乙基)色酮(3)、6-羟基-2-(2-苯乙基)色酮(4)、6-羟基-2-[2-(4-甲氧基苯)乙基]色酮(5)、8-氯-6-羟基-2-[2-(3-羟基-4-甲氧基苯)乙基]色酮(6)、8-氯-6-羟基-2-[2-(4-甲氧基苯)乙基]色酮(7)、oxidoagarochromone B(8)、4'-demethoxyaqusisnenone D(9)。其中,化合物6、7和9均为首次从柯拉斯那沉香中分离得到。活性测试结果显示,化合物1和2对乙酰胆碱脂酶具有一定的抑制活性,化合物2对人慢性髓原白血病细胞K562具有较弱的抑制作用。     

柯拉斯那沉香的化学成分研究

对柬埔寨野生柯拉斯那(Aquilaria crassna)沉香的化学成分和生物活性进行研究。实验采用多种柱色谱法对该沉香进行分离纯化;通过现代波普技术结合化合物理化性质对所得单体化合物进行结构鉴定,从柬埔寨野生柯拉斯那沉香共分离出12个化合物,分别鉴定为7α-H-9(10)-ene-11,12-epoxy-8-oxoeremophilane(1)、7β-H-9(10)-ene-11,12-epoxy-8-oxoeremophilane(2)、neopetasane (eremophila-9,11-dien-8-one)(3)、jinkoh-eremol(4)、(rel)-4β,5β,7β-eremophil-9-en-12,8β-olide(5)、诺卡酮(6)、11-hydroxy-valenc-1(10)-en-2-one(7)、(7S, 9S, 10S)-(+)-9-hydroxy-selina-4,11-dien-14-al(8)、5-羟基-2-[2-(4-甲氧基苯)乙烯基]色酮(9)、5-羟基-6甲氧基-2-(2-苯乙基)色酮(10)、6-甲氧基-2-(2-苯乙基)色酮(11)、5-羟基-6甲氧基-2-[2-(4-甲氧基苯)乙基]色酮(12)。其中化合物1～8为倍半萜类化合物,化合物9为2-(2-苯乙烯基)色酮类化合物,化合物10～12为2-(2-苯乙基)色酮类化合物。且化合物2～11均是首次从柯拉斯那沉香分离。采用Ellman比色法对单体化合物进行乙酰胆碱酯酶抑制活性的测定,活性测定结果表明化合物1～3和12具有乙酰胆碱酯酶抑制活性。     

柳叶拟沉香所产沉香的化学成分研究

采用ODS、硅胶、Sephadex LH-20等柱色谱技术从瑞香科(Thymelaeaceae)拟沉香属(Gyrinops)植物柳叶拟沉香(Gyrinops salicifolia Ridl)根部所产沉香中分离得到8个2-(2-苯乙基)色酮类化合物,运用波谱学方法解析鉴定为:2-(2-苯乙基)色酮(1)、5,8-二羟基-2-(2-苯乙基)色酮(2)、5,8-二羟基-2-[2-(4-甲氧基苯)乙基]色酮(3)、6,8-二羟基-2-(2-苯乙基)色酮(4)、6-羟基-7-甲氧基-2-[2-(4-羟基苯)乙基]色酮(5)、6-甲氧基-7-羟基-2-[2-(3-羟基-4-甲氧基苯)乙基]色酮(6)、6-羟基-7-甲氧基-2-[2-(3-羟基-4-甲氧基苯)乙基]色酮(7)和6-羟基-2-[2-(3-甲氧基-4-羟基苯)乙基]色酮(8)。以上化合物均为首次从拟沉香属植物所产沉香中分离得到。采用Elman比色法对全部化合物进行活性测试,结果表明化合物2~4、7对乙酰胆碱酯酶具有一定的抑制活性。     

柯拉斯那沉香的生物活性成分研究

为了解柯拉斯那(Aquilaria crassna)的化学成分,从其所产沉香中分离得到10个化合物,经波谱分析分别鉴定为:6,8-羟基-2-(2-苯乙基)色酮(1),6,8-二羟基-2-[2-(4-甲氧基苯)乙基]色酮(2),rel-(1a R,2R,3R,7b S)-1a,2,3,7b-tetrahydro-2,3-dihydroxy-5-(2-phenylethyl)-7H-oxireno[f][1]benzopyran-7-one(3),rel-(1a R,2R,3R,7b S)-1a,2,3,7b-tetrahydro-2,3-dihydroxy-[2-(4-methoxyphenyl)-ethyl]-7H-oxireno[f][1]benzopyran-7-one(4),rel-(1a R,2R,3R,7b S)-1a,2,3,7b-tetrahydro-2,3-dihydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)-ethyl]-7H-oxireno[f][1]benzopyran-7-one(5),oxidoagarochromone B(6),oxidoagarochromone C(7),(5S,6R,7S,8R)-2-[2-(3′-hydroxy-4′-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone(8),6,7-cis-dihydroxy-2-(2-phenylethyl)-5,6,7,8-tetrahydrochromone(9),N-trans-feruloyltyramine(10)。化合物3~5和8~10为首次从柯拉斯那沉香中分离得到。化合物1,3,6,7,9和10对乙酰胆碱酯酶具有一定的抑制活性,化合物4对人慢性髓原白血病细胞株K-562和人胃癌细胞株SGC-7901均具有较小的抑制作用,化合物1和3对人肝癌细胞株BEL-7402也有抑制活性。     

海南国产沉香的化学成分研究

从国产沉香(Aquilaria sinensis)的95%乙醇提取物中分离得到6个化合物,经波谱数据分析,分别鉴定为3,3'-(3-hydroxypropane-1,2-diyl)diphenol(1)、guaiacy lacetone(2)、6-羟基-2-(4'-羟基-2-苯乙基)色酮(3)、6-羟基-2-(2-羟基-2-苯乙基)色酮(4)、6-羟基-2-(2-苯乙基)色酮(5)和5α,6β,7α,8β-四羟基-2-(4'-甲氧基-2-苯乙基)-5,6,7,8-四氢色酮(6)。其中化合物1为新化合物,化合物3为首次从国产沉香中分离得到。     

通体结香技术产沉香的2-(2-苯乙基)色酮类化合物及其抗炎活性研究

对通体结香技术诱导白木香形成的沉香化学成分及其抗炎活性进行研究。采用液相和色谱技术进行分离纯化,从沉香中得到10个2-(2-苯乙基)色酮类化合物,通过理化常数和波谱分析分别鉴定为:2-(2-phenylethyl)chromone(1)、6-methoxy-2-(2-phenylethyl)chromone(2)、5-hydroxy-6-methoxy-2-(2-phenylethyl)chromone(3)、6,7-dimethoxy-2-[2-(4'-methoxyphenyl)ethyl]chromone(4)、7-Hydroxy-6-methoxy-2-[2-(4'-methoxyphenyl)ethyl]chromone(5)、2-[2-(4'-methoxyphenyl)ethyl]chromone(6)、6,7-dimethoxy-2-[2-(3'-hydroxy-4'-methoxyphenyl)ethyl]chromone(7)、6,7-dimethoxy-2-(2-phenyl ethyl)chromone(8)、6,8-dihydroxy-2-[2-(3'-hydroxy-4'-methoxyphenyl)ethyl]chromone(9)、6-hydroxy-2-[2-(4'-methoxyphenyl)ethyl]chromone(10)。结合脂多糖介导RAW264.7细胞模型评价其抗炎活性。其中,化合物2~4和10具有显著的抗炎活性,IC50值分别为5.31±0.75,5.57±0.62,0.57±0.02,3.78±0.64μM。化合物5为首次从白木香产沉香中分离得到,所有化合物均为首次从通体结香技术所产沉香中所得,为其品质评价提供了基础依据。     

降香化学成分研究CSCD

为研究降香(Dalbergiae Odoriferae Lignum)的化学成分,应用硅胶、Sephadex LH-20、高效液相色谱等色谱技术进行分离纯化,从降香的乙醇提取物中分离得到10个化合物,运用波谱学方法分别鉴定为isopterocarpolone(1)、紫檀醇(2)、4,7-二甲氧基-2′-羟基异黄酮(3)、7,4′-二甲氧基异黄酮(4)、3-(4-羟基-2-甲氧基苯基)-7-甲氧基-4 H-色烯-4-酮(5)、(3 R)-驴食草酚(6)、(3 R)-3,2′-二羟基-7,4′-二甲氧基二氢异黄酮(7)、美迪紫檀素(8)、(6a S,11a S)-高紫檀素(9)、3,9-二甲基-6 H-苯并呋喃[3,2-c]色烯-6-酮(10)。化合物1、2、4、5、7为首次从降香中分离得到。化合物1、6、8和9具有α-葡萄糖苷酶抑制活性,IC_(50)值分别为366.77±1.46、113.11±0.87、56.21±1.01、92.63±0.91μmol/L,强于阳性对照阿卡波糖(528.00±2.60μmol/L)。     

镰形棘豆化学成分的研究

采用柱层析(CC)、短柱减压层析、重结晶等分离手段,从镰形棘豆乙醇提取液中分得7个已知化合物,经波谱分析鉴定为N-苯甲酰基-2-苯基乙胺(1),N-肉桂酰基-2-苯基-2-乙胺(2),N-苯甲酰基-2-羟基-2-苯基乙胺(3),2′-羟基-4′-甲氧基查儿酮(4),7-甲氧基黄烷酮(5)、5-羟基-7-甲氧基黄烷酮(6),β-谷甾醇(7).化合物1～3、5、6均为首次从该植物中分到.药理实验表明化合物4,5对人胃癌细胞株SGC有较强的细胞毒活性,IC50分别为3.61和6.11 μg/mL.     

白木香悬浮培养细胞中2-(2-苯乙基)色酮化合物的诱导形成

白木香是我国生产沉香的唯一植物资源,为研究其中次生代谢产物的生物合成,从国产沉香中分离并鉴定了4种已知的2-(2-苯乙基)色酮化合物,实验中以此作为标准品,以白木香根悬浮培养细胞为材料,黄绿墨耳真菌提取物为诱导子,首次在组织培养物中成功诱导了2-(2-苯乙基)色酮化合物的产生,为研究中药沉香活性成分2-(2-苯乙基)色酮化合物的生物合成建立了一个试验体系。     

美花石斛化学成分及其护肤活性研究

本文研究美花石斛(Dendrobium loddigesii)的化学成分及其护肤活性。采用色谱法从美花石斛粗提物中分离得到12个化合物,利用波谱学方法分别鉴定为拖鞋状石斛素(1)、2,4,7-三羟基-9,10-二氢菲(2)、3,6,9-三羟基-3,4-二氢蒽-1(2H)-酮(3)、3,5′-二甲氧基-3′,4,9′-三羟基-7′,9-环氧-8,8′-木酚素(4)、5-(4-羟基-3-甲氧基苯乙基)-2-(4-羟基-3-甲氧基苯基)苯并二氢呋喃-3,7-二醇(5)、5-(4′′-羟基-3′′-甲氧基苯乙基)-2-(4′-羟基-5′-甲氧基苯基)-7-甲氧基苯并二氢吡喃-3-醇(6)、丁香脂素(7)、异香草醛(8)、松柏醛(9)、2-甲氧基-5-羟甲基苯酚(10)、二氢松柏醇(11)、4-羟基-3-甲氧基苯乙醇(12)。其中化合物3～5、7～12为首次从美花石斛中分离得到;化合物1、2、6(100μg/mL)有一定的自由基清除活性(>80%);化合物2(10μg/mL)有一定促胶原蛋白分泌活性(>20%)。结果显示从美花石斛的茎中分离得到了12个化合物,3个表现出良好的护肤活性。     

Production of 2-(2-phenylethyl) Chromones in Cell Suspension Cultures of <Emphasis Type="Italic">Aquilaria sinensis</Emphasis>

2-(2-Phenylethyl) chromones are the major constituents responsible for the quality of agarwood, which is one of the most valuable non-timber products used as incenses, perfumes, traditional medicines and other products. In this study, cell suspension culture of Aquilaria sinensis (Lour) Gilg was used to monitor the eliciting effects of crude fungal extracts on cell growth and chromones production. Crude extracts of Melanotus flavolivens (B. etc) Sing. prepared with different solvents were used to elicit the production of 2-(2-phenylethyl) chromones in cell suspension cultures of A. sinensis. Four 2-(2-phenylethyl) chromones,␣6,7-dimethoxy-2-(2-phenylethyl) chromone (1), 6,7-dimethoxy-2-[2-(4′-methoxyphenyl)ethyl] chromone (2), 6-methoxy-2-[2-(4′-methoxyphenyl)ethyl] chromone (3) and 6-methoxy-2-(2-phenylethyl) chromone␣(4),␣were detected by LC–MS in the cell suspension culture of A. sinensis elicited with crude extracts of M. flavolivens. Three hundred and seventy eight, 196 and 31 μg g⁻¹ DW of 2-(2-phenylethyl) chromones were obtained in the cell cultures induced by water extracts, 50 and 95% ethanol extracts of M. flavolivens, respectively. The results show that water-soluble materials in the crude extracts are the main components inducing the production of 2-(2-phenylethyl) chromones in the cell cultures.     

Production of 2-(2-phenylethyl)chromones in <Emphasis Type="Italic">Aquilaria sinensis</Emphasis> calli under different treatments

2-(2-Phenylethyl)chromones are main classes of aromatic compounds isolated from agarwood, the resinous portion derived from Aquilaria sinensis used as traditional medicine, incense and perfume. However, the mechanisms of biosynthesis of 2-(2-phenylethyl)chromones and agarwood formation are still unknown. Previous studies indicated that 6,7-dimethoxy-2-[2-(4′-methoxyphenyl)ethyl]chromone (AH₈) and 6,7-dimethoxy-2-(2-phenylethyl)chromone (AH₆) were more sensitive to salt stress and can be used as markers to analyze the production of 2-(2-phenylethyl)chromones. In this study, the content of AH₆ and AH₈ was analyzed by an AB Sciex 5500 Qtrap mass spectrometer and the congeners of 2-(2-phenylethyl)chromones were detected by LC-DAD-IT-TOF-MS system in A. sinensis calli under various abiotic stresses and hormone treatments. Among the abiotic stresses, salt and drought stress remarkably increased the production of AH₆ and AH₈, and could induce 41 and 23 species of 2-(2-phenylethyl)chromones, respectively. However, cold treatment has little influence on the production of 2-(2-phenylethyl)chromones. Ion stresses induced by KNO₃, CaCl₂, and (NH₄)₂SO₄ also significantly increased the content of AH₆ and AH₈, and could induced 14, 18, and 14 congeners of 2-(2-phenylethyl)chromones, respectively. Exogenous hormones including MeJA, SA and ABA induced a small amount of 2-(2-phenylethyl)chromones in calli within 20 days, while 6, 5, and 7 species of 2-(2-phenylethyl)chromones were detected after MeJA, SA and ABA treatment, respectively. Our study would provide solid basis for further research on biosynthesis of 2-(2-phenylethyl)chromones and agarwood formation.     

白木香果实化学成分研究

运用柱色谱技术从白木香(Aquilaria sinensis (Lour.) Gilg)果实中分离得到7个化合物,经波谱解析和理化性质分别鉴定为: 3-吲哚甲酸(1)、6-羟基-2-[2-(4-羟基苯基)乙基]色原酮(2)、芫花素(3)、4', 5-二羟基-3',7-二甲氧基黄酮(4)、洋芹素-7,4'-二甲醚(5)、 β-谷甾醇(6)和胡萝卜苷(7)。其中化合物1为首次从瑞香科沉香属植物中分离得到。     

宁夏枸杞根和茎的化学成分及抗炎活性研究

研究宁夏枸杞(Lycium barbarum L.)根部和茎部的化学成分。采用硅胶柱、ODS开放柱、Sephadex LH-20葡聚糖凝胶柱及半制备反相高效液相等色谱手段,对宁夏枸杞根和茎部乙醇提取物的石油醚部位及乙酸乙酯部位化学成分进行分离纯化,根据其理化性质以及波谱数据鉴定得到12个化合物,分别为N-[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]-3-(4-methoxyphenyl)prop-2-enamide(1)、3-(4-hydroxy-3-methoxy phenyl)-N-2-(4-hydroxyphenyl)-2-methoxyethyl]acrylamide(2)、N-trans-coumaroyloctopamine(3)、(E)-2-(4,5-dihydroxy-2-{3-[(4-hydroxyphenethyl)amino]-3-oxopropyl}phenyl)-3-(4-hydroxy-3,5-dimethoxyphenyl)-N-(4-acetamidobutyl)acrylamide(4)、1,2-dihydro-6,8-dimethoxy-7-hydroxy-1-(3,4-dihydroxy-phenyl)-N1,N2-bis[2-(4-hydroxyphenyl)ethyl]-2,3-naphthalene dicarboxamide(5)、(+)-syringaresinol(6)、zhebeiresinol(7)、(±)-eriodictyol(8)、isovanilin(9)、5,5′-dimethoxybiphenyl-2,2′-diol(10)、p-hydroxyphenethyltrans-ferulate(11)、E-ferulic acid hexacosyl ester(12),所有化合物均为首次从该植物中分离得到。此外,采用MTT法和抑制一氧化氮(NO)生成实验,从细胞毒活性和抗炎活性两方面评估了化合物的生物活性。结果表明,化合物2具有显著的抗炎活性,其IC50值(17.00±1.11μmol/L)小于阳性对照药槲皮素的IC50值(17.21±0.50μmol/L)。     

Tetronic acid and diarylpropanes from Iryanthera elliptica

The trunk wood of Iryanthera elliptica Ducke (Myristicaceae) contains, besides 2-(ω-piperonyltridecyl) -4-methylidenetetronic acid (iryelliptin), three biogenetically related compounds: (±)-7,4′-dihydroxy-3′-methoxyflavan, 1-(4′-hydroxy-2′-methoxyphenyl)- 3-(4″-hydroxy-3″-methoxyphenyl)-propane and spiro-[3-methoxy-2,5-cyclohexadien-1.1′-6′,7′- dihydroxy-5′-methoxy-1′,2′,3′,4′-tetrahydronaphthalen]-4-one-(spiroelliptin). Spiroelliptin rearranges upon methylation to 2,2′-trimethylene-3,4,5,4′,5′-penta-methoxybiphenyl.     

Neoflavonoids and the cinnamylphenol kuhlmannistyrene from Machaerium kuhlmannii and M. Nictitans

The trunkwood of Machaerium kuhlmannii contains methyl palmitate, 3-O-acetyloleanolic acid and sitosterol; the benzene derivatives 2,3-dimethoxyphenol, 2,6-dimethoxyphenol, 2-hydroxy-3-methoxyphenol, 2,3-dimethoxybenzaldehyde and methyl 3-(2-hydroxy-4-methoxyphenyl)-propionate; the isoflavonoids formononetin and (6aS,11aS)-medicarpin; the neoflavonoids (R)-3,4-dimethoxydalbergione, (R)-3,4-dimethoxydalbergiquinol, kuhlmanniquinol [(R)-3-(4-hydroxyphenyl)-3-(5-hydroxy-2,3,4-trimethoxyphenyl)-propene], dalbergin, kuhlmannin (6-hydroxy-7,8-dimethoxy-4-phenylcoumarin) and kuhlmannene (6-hydroxy-7,8-dimethoxy-4-phenylchrom-3-ene), as well as the cinnamylphenol kuhlmannistyrene [Z-1-(5-hydroxy-2,3,4-trimethoxybenzyl)-2-(2-hydroxyphenyl)-ethylene]. Five of these compounds, in addition to (R)-4′-hydroxy-3,4-dimethoxydalbergione, were also isolated from a trunkwood extract of M. nictitans. Structural assignments were confirmed by chemical interconversion and by the synthesis of (±)-kuhlmanniquinol.     

Chemical Constituents of Phacellaria compressa Benth.

Two new compounds, 1-（3-methoxy-4-hydroxyphenyl）-3-（3,5-dimethoxy-4-hydroxyphenyl）-propane （1） and 5, 7, 3＇-trlmethyoxyflavan-4＇-O-β-D-glucopyranoslde （2） were Isolated from the ethanol extract of the dried aerial parts of Phacellarla compressa Benth., together with 2,3-bis[（4-hydroxy-3,5-dimethoxyphenyl）-methyl]-1,4- butanedlol （3）, ethyl 3,4,5-trlhydroxybenzoate （4）, methyl 3, 4, 5-trlhydroxybenzoete （5）, β-sltoeterol （6）, 5, 7, 3＇, 4＇- tetrahydroxyfiavan （7）, lupeol （8）, zhebelreslnol （9）, quercetln-3-O-α-L-rhamnopyranoslde （10）, （＋）-cetechin （11）, betulln （12）, β-daucosterol （13）, （＋）-sydngareslnol （14）, scopoletln （15）, and proxlmadlol （16）. The structures of these compounds were determined by spectral evidence or by comparing them with authentic samples. Compound 9 showed α-amylase Inhibitory activity of 57.55% at a concentration of 50 μg/mL.     

Triterpenes and lignans from the leaves of Styrax tonkinensis

Two triterpenes (1 and 2) and eight lignans (3–10) were isolated from the ethyl acetate-soluble fraction of the leaves of Styrax tonkinensis (Pierre) Craib ex Hartw (Styracaceae). Their structures were established as ursolic acid (1), pomolic acid (2), 3,3′-bis(3,4-dihydro-6-methoxy-2H-1-benzopyran) (3), rac-(8α,8′β)-4,4′-dihydroxy-3,3′-dimethoxylignan-9,9′-diyldiacetate (4), (-)-secoisolariciresinol (5), (+)-pinoresinol (6), 4,4′-dihydroxy-3,3′-dimethoxy-9-ethoxy-9,9′-epoxylignan (7), (2S,3R, 4R)-4-[1-ethoxy-1-(4-hydroxy-3-methoxy)phenyl]methyl-2-(4-hydroxy-3-methoxy)phenyl-3-hydroxymethyl-tetrahydrofuran (8), (-)-neo-olivil-(9-O-9″)-seco-isolariciresinol (9) and isolariciresinol (10) based on MS, ¹H-and ¹³C-NMR spectral data. All these compounds (1–10) were firstly isolated from this plant, and compounds 2–5 and 7–9 were reported from the Styrax genus for the first time. Furthermore, the chemotaxonomic significance of the isolated compounds was discussed.